first date advice

I've been stewing on this for awhile -- a student asked me about what to remember when going on or asking someone out for a first date. So here goes...

Disclaimer: of course I can't say everything that could possibly be said about this. But, what follows is what came to my mind. Please also ask wise, discerning people you know in your life about this too.

-A wise friend once said to me: "Dates can either be perfect, or they can be interesting. And truth be told, interesting is way easier to pull off than perfect." 

So do not aim for perfect. Aim for sufficiently interesting.

-Ask clearly that you'd like to hang out, and not just as friends. 

Yes, it's bold. Yes, it's a bit frightening. But it's also clear, and people appreciate clarity. Might as well put your intentions out there. Possibly getting let down sooner > possibly getting let down later.

-Keep the vibe of shooting your shot purposeful, concise, yet casual. Act as though you've thought it through, and it makes absolute logical sense from your perspective. "You're fun to spend time with, I enjoy talking with you, so asking you out is a no-brainer for me. What do you say?"

-If they decline: say OK. And if/when you see them around after the fact, do your best to relate to them as respectfully and innocuously as possible. You don't need to show them the same frenetic excitement as you might have done before the ask, but it's still wise to interact amiably.

You, giving them your usual head nod

If they decline, part II: Odds are good they're used to getting a weird vibe after turning someone down, so try to avoid that.

You treating them with respect will show maturity, and may perplex them (in a good way).

Why this matters, practically speaking: let's say you ask, they decline, and you do treat them with follow-up respect, normalcy, and friendliness. But then later on, a friend of theirs catches your interest. What will the first person say if/when asked about you? If you treat them maturely, they'll have a good report to share : "They weren't really my type, but they were cool about it". That says a lot.

-Food: for initial times hanging out, lunches (or brunches) are easier than dinners. It feels like there's less on the line if the rizz isn't quite fully blooming at first, but it has potential. 

And it's less time to fill with conversation.

-A word on complimenting physical appearance: For the first few times hanging out or anything like that, avoid complimenting how gorgeous they look, or how beautiful they are, etc. That comes across as way WAY too forward.

What you can do instead: specifically compliment something about what they're wearing. Maybe it's earrings, or their shoes, or their jacket, or fingernail polish, or their shirt, or bracelet. Whatever. Especially if it's something unique. You can also ask for the story of how and where they acquired said item. It gives you something to talk about. It shows that you're attentive. And it's a compliment. But it's a compliment that doesn't give a weird vibe.

-If you're doing the asking for the date, you probably should offer to pay. My reasoning has nothing to do with any potential gender expectations. It's because of this unavoidable truth: the potential downsides of offering to pay beat the potential downsides of not offering to pay.

-For example, one potential downside of not offering to pay: let's say the person that you asked out has a friend you meet later, and that person really could be someone suitable for you. You'd much rather have the talk about you be 'he wasn't really my type, but our hanging out was fine' then have them say 'eh, he asked me out, but he didn't even offer to pay'.

-If you'd like to pay for the date, please say so before anyone else (restaurant, ticket agent, cashier) asks. If the other person resists this, a possible way through is to ask if they have any cash on them. If they do, tell them that you'd like to pay, and ask them if they can leave the tip. Or if you're getting ice cream after that, could they pay for that.

If they still insist on paying for their portion, then let it be. This is not something you want to dwell on. Don't say "you pay the next time", that feels too presumptive.

-Does the person you're asking have any dietary allergies or restrictions? 

If so, and if y'all are going to grab a bite to eat, knowing beforehand what eateries can accommodate helps. And it makes you look considerate and thoughtful.

-If you're someone who likes to plan ahead, but also doesn't want to give off 'controlling' vibes, have a couple of date ideas in mind, all for which you're prepped. Float the options to the other person, and see what option toward which they react favorably. That way, they have a say too, but you're still able to think stuff through and plan.

People do like choices.

-Wear the clothes that you're most comfortable in, that also fit you well. Please make sure they're clean. Take a shower.

-Give your shoes a quick look. Taking three minutes to clean up your sneakers or polish your shoes makes a world of difference. If it's a first date, give strong consideration to not wearing flip-flops or anything that shows bare feet. Sheath the paws.

-Chew gum, take breath mints with you. It never hurts.

-Go easy on the cologne, or perfume. This scent is meant to be discovered, NOT ANNOUNCED. Spray it on your skin, not your clothes -- any decent body spray is formulated to interact with your body temperature.

-Take your phone, but do your best to not check it with them there.

-Steer clear of alcohol and/or mind-altering substances. This is generally decent advice, but especially so on a first date. 

-If you're taking your car, clean it out ahead of time, fill up the gas if needed.

That Raising Cane's to-go bag that's been on the front seat floorboard since your 10PM late snack run the other weekend? Throw it out.

That random hockey stick wedged in your backseat? Put it somewhere else.

The funk-y soccer cleats you keep in your backseat because it's convenient? Move them to the trunk.

Those used coffee cups you've been meaning to recycle but haven't yet? Today's recycling day.

The car doesn't need to look showroom new. It just needs to look (and smell) like you usually take care of it. You get the idea.

-If you need to borrow a car, work that out with a friend ahead of time. Put some gas back in the car after you're done with it (however much you used), as a courtesy.

-Let your friends know where you're going, and who you'll be with. Ask them to pray for you.

-Think ahead of time about what you might like to talk about, to keep conversation going. Easy, loose conversations take a studied sort of background effort to maintain. But they get easier with practice. Pro tip: people love to be able to answer questions brilliantly, ie questions about themselves, or about their past experiences, or about why they're into whatever they're into.

But also ... don't only ask questions. Too many could feel like an interview, so also come ready to talk about yourself, do some small talk. Questions should ideally morph into conversations.

A helpful book regarding good questions

-Don't talk about the ex. A first date is not the time for this, even if it's an innocuous, lighthearted story. There's so much other stuff to converse about. If the story is too good and too related to the moment to not share, then say it's about "a friend of yours" or "someone you went to school with."

-End the date concisely. If you're dropping them off, make the effort to walk them to the door, or to get them as close as possible to where you're dropping them off. Thank them for their time, tell them you enjoyed their company. Don't ask them out on another outing at the end -- give yourself (and them!) space to reflect on the time y'all spent together. Stay there until you see them successfully make entry into wherever they live.

-Then go decompress with your friends and/or trusted voices in your life. Resist your phone or updating your social media. Go radio silent on social media about the date.

-Send a text the next day to thank them for the time. If you send it too soon after the date, it feels like a pre-prepared auto-notification thank you. So wait on it. Keep the text short, sincere. We're all in a better mood and more rested in the morning, so send it in the mid-morning. 

And then do your best to not hover over your phone to see when a reply text arrives.

friends with an ex

"Of course we can still be friends." The last gasp of a dating relationship/situationship, etc.

Is trying to salvage a friendship worth your time? In time, maybe. Not always, though

Is it realistic? Well, that depends--

Is it just something nice that's said to show politeness? Usually. 

A few matters about this to point out, in no particular order (Dear Reader: please note, these principles and useful tips I've learned myself, usually the hard way -- happy to discuss further in person, as usual).

a) It's grueling to try to stay friends immediately after a breakup. Try to salvage a friendship -- not right away -- but way, way later. A wise rule of thumb: restoring a friendship cannot really start until the person most hurt and/or surprised by the breakup feels ready to do so.

b) Whether you're doing the breaking up, or being broken up with, no one can demand friendship. By friendship, I mean the effort to keep connection and to share life with another. Friendship is friendship because it's freely exchanged. So if you do not want to be friends, that's acceptable. The other person doesn't have to agree.

b) If you hope this 'let's stay friends' sentiment will lead you to someday get back together, please note: that's a harrowing place for your heart to perch and to wait. Don't let your hopes wander too far out onto that branch.

c) One (or both) of y'all will need quality time ... apart. No contact, don't reach out, social media unfollowing/ muting, stay away from where they frequent, no spending time together --- these are all wise steps to take. It often compares to weaning yourself off an addiction. So go your own way (and call it another lonely day).

d) Friends with benefits: an awful, counterproductive, dignity-marring, heart-damaging, dumb idea. Please don't do it. You deserve so much better. Part of reminding yourself of the truth (that you deserve better) is to steadfastly stay far, far, far away from whatever could never co-exist with that truth.

e) You will feel some pangs -- of desire, angst, or heartache -- when you see your ex. 

Ouch. 

A best friend of mine taught me that this does NOT mean we still want to be with them. It usually happens because we've trained ourselves to respond a certain way when we see that person. Ergo, it takes time to undo our conditioned response, and to think of them differently. 

Give yourself that time.

e) The first few times of being around an ex will feel weird and clumsy. That's normal.

f) If you want to work toward being friends, do yourself a favor: do not ask them if they're dating or in a situationship with anyone. You don't need to know. This is tea you need not try to spill.

g) We all suffer through moments when our emotions ping around our brains at hyper-speed ... when we can't resist believing every absurd-anxious, half-baked thought we have about how we suck, and how no one could ever really love us. 

"Oh, that's not just me?!?" you may think. 

It's not.

Your brain will entertain this crooked frame of thinking at times. It sucks. And it won't last. But, to get your head straight, you'll need to talk it out. With a friend.

When your perspective warps in this way, try your level best to not seek support from your ex (nor from any of your ex's friends). Fall apart and piece yourself back together in a place, and with people, loyal to you ... safe for you ... relatively uncomplicated for you ... who won't gossip about you.

i) Pro Tip: If, soon after the breakup, you're with a group of people, and the other person is also there or will be there, try to arrive first. This way, you can find people to interact with who will keep your attention occupied and talking about anything else.

j) Pro Tip #2: If you're with a group of people, and the other person is there ... leaving too early > staying too long. Plan your exit. Leave when you plan to leave. Be concise and cheerily bland with saying goodbye to the group, and get out.

k) If the ex sends a message/calls/sends a notification ... don't respond until about a full day later, at minimum. It's not mean. It's wise. 

This particularly holds true for messages received say between 10:32AM-3:47AM). In a word: everyone is dumber in the later evening hours. Everyone is less mentally/emotionally sharp after midnight. You are too.

Eventually, keeping a friendship with an ex does become easier. You may not stay in touch with this person all your life. But it can get to a place where -- if you see each other somewhere -- it can be cordial. Respectful. Not a big deal.

And ... in time ... if being friends works well, you might become some version of an unproblematic ex for them. Someone trusted. You become someone your ex wouldn't mind introducing to their current partner, or future spouse. You can be in the same space, it isn't weird, it doesn't get physical, and you're content.

That's a sweet place to be. But it takes time. It takes effort, and boundaries. It takes grace, and it takes forgiveness to get there.